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Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters

Leyah A. Schwartz, Michael Holmes, Gilmar A. Brito, Théo P. Gonçalves, Jeffery Richardson, J. Craig Ruble, Kuo-Wei Huang, Michael J. Krische*

*Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States, Email: mkrischemail.utexas.edu

L. A. Schwartz, M. Holmes, G. A. Brito, T. P. Gonçalves, J. Richardson, J. C. Ruble, K.-W. Huang, M. J. Krische, J. Am. Chem. Soc., 2019, 141, 2087-2096.

DOI: 10.1021/jacs.8b11868 (free Supporting Information)



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Abstract

An Ir-catalyzed reductive coupling of diverse 1,1-disubstituted allenes with fluoral hydrate in the presence of 2-propanol provides CF3-substituted secondary alcohols with acyclic quaternary carbon-containing stereodiads.  A stereochemical model shows that the ortho-CH2 group of the cyclometalated iridium-PhanePhos complex plays a key role in directing diastereo- and enantioselectivity.


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Key Words

α-trifluoromethyl alcohols


ID: J48-Y2019